Dimethyl Sulfoxide → HCID 59456013, compound

HRID 1892951Notes

Reaction equation

HRID 1892951 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH3:12])[N:4]([CH2:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])[N:3]=1.[CH3:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1.CS(C)=O>N1C=CC=CC=1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[C:2]([NH:1][S:29]([C:27]1[S:28][C:24]([CH3:23])=[CH:25][CH:26]=1)(=[O:31])=[O:30])=[N:3][N:4]2[CH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 124001125-Methylthiophene-2-sulfonyl chlorideHCID 580544693-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide

Product 1

HCID 59456013HCID 59456013, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-{[3-Amino-4-(methyloxy)-1H-indazol-1-yl]methyl}benzamide (for a preparation see Intermediate 12) 22 mg, 0.07 mmol) was dissolved in pyridine (1.6 mL) and added to 5-methyl-2-thiophenesulfonyl chloride (20 mg, 0.1 mmol). The reaction mixture was shaken at room temperature for 5 min and then stood overnight at room temperature. DMSO (0.2 mL) was added to the reaction mixture and purified by MDAP on Atlantis column using Acetonitrile Water with a Formic acid modifier. The solvent was evaporated in vacuo using the Genevac to give the title compound (14.2 mg, 44%) LCMS (System A) RT=0.92 min, ES+ve m/z 457 (M+H)+.

Workup

  1. waitstood overnight at room temperature
  2. custompurified by MDAP on Atlantis column
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d35033a3bccc42b3ae395e1e0b92c99a
Source dataset
uspto-grants-2013_08
Patent number
US08507543B2

Reaction notes

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